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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Identify the species that is predicted to be aromatic according to Hückel's rule. (I) (II) (III)

Options

  1. AOnly (I)
  2. BOnly (III)
  3. COnly (II)
  4. DBoth (I) and (II)

Correct answer

C. Only (II)

Step-by-step solution

According to Hückel's rule, a compound is aromatic if it is cyclic, planar, completely conjugated, and contains (4n + 2) electrons. In structure (I), the boron atom is sp^2 hybridized and possesses an empty p-orbital, allowing continuous conjugation. The system contains 4 electrons, which follows the 4n rule ( n=1 ). Thus, it is antiaromatic. In structure (II) (pyrrole), the nitrogen atom is sp^2 hybridized and its lone pair of electrons resides in an unhybridized p-orbital that participates in the ring's conjugati

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